D&D 5E How to handle a shapechanging Mermaid

3.) Everything below her waist automatically falls off on the ground. Any armor worn on her legs, boots or shoes, and pants ends up on a pile on the floor. Its probably more "realistic" than trying to explain how her gear merges into her, but everytime she shifts back; she's naked from the waist down. (I suppose a robe or dress would still work though).
4.) As 3, but unless she takes the time to take off said items, they could be ruined. (Clothes ripped, buckles break, shoes tatter). Most "realistic" type of transformation, but least "fun".

So I'm looking for some advice on how to handle this transformation in the most logical (yet fair) way.

We have a werebear in our group. He is a druid, a rather large man.
For being a werebear he gets many benefits - advantage on perception checks (smell), higher strength score (which includes carrying and lifting as we play encumbrance), ability to climb better, incredible regeneration rate (a little different than complete immunity), and the ability to transform into bear and hybrid form.

The following are his disadvantages - shapechange destroys restrictive clothing worn (so he wears a loose pants and no armour), animals generally shy away or are fearful as they pick up his lycanthropic nature, he eats double the quantity of food a normal person would (given his size and lycanthropic nature - explaining it has an accelerated metabolism)

So considering your options, I would definitely say number 4, unless she wears looser clothing then 3 is also an option. For instance a dress with sandals/light boots - you could say the transformation pulls the foot up before joining to the other and then extends to form a tail. Legging/pants would have to be taken off, destroyed and/or do physical damage to her when transforming.
 

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Okay, I have a friend who is interested in playing a merfolk. Rather than tell her about how bad tails are for dungeon crawling,

Left field idea: What if it tails weren't an obstacle to dungeon crawling? What if she just moves around on a tail like a yuan-ti?

For inspiration, you could look up "Nami League of Legends" on Youtube. She's a land based mermaid.

Everything below her waist automatically falls off on the ground

My inner 14-year-old votes for this, however.

"Even before she can get her knickers on, I've seen everything. I've seen it all." - Patrick Stewart
 

I'd allow the player to choose which items merge and become nonfunctional, and which stay unchanged. Allow her to breathe air and water in either form, but in mermaid form she gets a swim speed of 40 or so.
 

Well, we'll talk tonight. This gave me a lot to think on.
The player is fairly new to the game, but loves mermaids so I thought it would be a good hook to get her excited. I'm leaning on rather making her a subtype of merfolk that grows legs, I might just make her a special merfolk that has a magical blessing/ritual that changes her, allowing her some modesty.
I'll update on what gets done tonight.
 



I'd disallowed it unless I was planning to run way more water related scenarios than usual.

On the other hand, having such a character may lead to more water-related scenarios, so rather than have the PCs fit the campaign, the campaign fits the PCs.

That said, if I was doing a heavily water-based game (like pirates on the high seas) I'd actually be more hesitant; water breathing is a powerful feature when you're constantly surrounded by water, less so when you stumble upon an underground lake or waterfall.
 

You might want to consider adding an extra restriction like the mermaid has to change back and fully immerse herself in water once a week (can be a bath or river). If she doesn't, she starts suffering some sort of status effect until she is able to get back into the water.

This re-emphasizes the mermaids connection to the water, and adds a small price to the ability to have legs.
 

That said, if I was doing a heavily water-based game (like pirates on the high seas) I'd actually be more hesitant; water breathing is a powerful feature when you're constantly surrounded by water, less so when you stumble upon an underground lake or waterfall.

I actually have an entirely water-based campaign and all the mer-races get this shapeshift feature naturally, however there is time limit on how long they can go without being in the water.
 


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